Like the user case above, when there are some unmovable files on the target partition, the shrinking volume process might be unable to continue smoothly. Generally, users can shrink a volume via the Windows built-in Disk Management, which provides the “Shrink Volume” and “Extend Volume” options. However, in some cases, it cannot shrink volume successfully as you expected. Shrinking volume can generate an unallocated space, with which you can create new partition or extend another existing partition in Server 2016. I have emptied the trash bin but it did not help with this issue. It has something to do with the unmovable files. I shrinked it to this size from 300GB, but now I cannot shrink it anymore. I have D: drive that is 200G and about half of it is empty space.